Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 8 - Reactions of Alkenes - Problems: Problem 8-22 c


The following synthetic conversion can be obtained through addition of $H_2SO_4$ with heat and then Halohydrins mechanism.

Work Step by Step

The reaction of $H_2SO_4$ in presence of heat gives a double bond by deprotonating OH. Then on this double bond the halohydrin mechanism is performed. The mechanism that gives this product is the addition of Halohydrins: 1) Electrophilic attack forms a chloronium ion. 2) Back-side attack by water on the most substituted carbon opens the chloronium ion. 3) Water removes a proton to give the chlorohydrin. Product + enantiomer formed.
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